Aldol reactions on solid phase. Sc(OTf)(3)-catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol,beta-hydroxy carboxylic acid, and beta-hydroxy aldehyde libraries

被引:48
作者
Kobayashi, S
Hachiya, I
Yasuda, M
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
基金
日本学术振兴会;
关键词
D O I
10.1016/0040-4039(96)01158-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldol reactions on solid phase have been achieved. In the presence of a catalytic amount of scandium triflate (Sc(OTf)(3)), polymer-supported silyl enol ethers reacted with aldehydes to afford the corresponding beta-hydroxy thioester derivatives, which were reduced to I,3-diol and beta-hydroxy aldehyde derivatives, or hydrolyzed to beta-hydroxy carboxylic acid derivatives. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5569 / 5572
页数:4
相关论文
共 18 条
[1]  
BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, V1, P85
[2]  
Colvin E. W., 1981, SILICON ORGANIC SYNT, P165
[3]  
FLEMING I, 1980, CHIMIA, V34, P265
[4]   Organic chemistry on solid supports [J].
Fruchtel, JS ;
Jung, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42
[5]   APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].
GORDON, EM ;
BARRETT, RW ;
DOWER, WJ ;
FODOR, SPA ;
GALLOP, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401
[6]   Solid-phase organic reactions: A review of the recent literature [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, D .
TETRAHEDRON, 1996, 52 (13) :4527-4554
[7]  
KOBAYASHI S, 1994, SYNLETT, P689
[8]   Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library [J].
Kobayashi, S ;
Hachiya, I ;
Suzuki, S ;
Moriwaki, M .
TETRAHEDRON LETTERS, 1996, 37 (16) :2809-2812
[9]   SCANDIUM TRIFLUOROMETHANESULFONATE (SC(OTF)3) - A NOVEL REUSABLE CATALYST IN THE DIELS-ALDER REACTION [J].
KOBAYASHI, S ;
HACHIYA, I ;
ARAKI, M ;
ISHITANI, H .
TETRAHEDRON LETTERS, 1993, 34 (23) :3755-3758
[10]  
KOBAYASHI S, 1993, SYNLETT, P472